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Chestertown, Maryland: An American Hometown for More than 350 Years

July 28, 2024 2pm - 4pm

There's nothing like going to the movies on a hot summer day. Join us to watch a 1995 film documenting life in Chestertown at two moments in our history.

Our new site is still under construction. Stay tuned!

The Key to Kent County History

More than an exhibit and more than a digital archive, this online resource is an ever-expanding portal to information about Kent County, Maryland, history. Beginning with a simple timeline of our history that connects users to additional information and topics, this section of the Historical Society of Kent County website will expand as we discover new links and research materials; write new material about the people, places and stories of our county; and add new items to our collection and online catalog. Together, these resources will allow students of history and researchers to get a sense of the richness of Kent’s history.

Using the Key to Kent County History: The Key to Kent County History is divided into eight time periods, from settlement through the present day. An introductory paragraph summarizes each time period, with additional information on a variety of subtopics below. You may explore as much of this information as you choose. Navigate to various time periods using the menu on the right.

In addition, each time period contains a collection of resources, from articles, websites and primary source materials which can be found on the internet, to links on information in the Society’s own catalog. A selection of images is available, as are articles based on original research by the Society, “Articles and Information.” These resources can be accessed using the menu bar at the top of each time period.

Look for additional resources to be added to this website in the near future. If you would like to suggest a resource available on the internet, please send the link information to

Exploration and Settlement: The 1600s

Introduction: “Heaven and earth never agreed better to frame a place for man’s habitation,” wrote Captain John Smith of the Eastern Shore, as he explored the Bay and its inlets “fit for harbor and habitation.” In 1608, Smith explored the Sassafras River, landing at a Tockwogh village near present-day Rock Hall. Twenty-six years later, Cecilius Calvert, the second Lord Baltimore, sent the ships Ark and Dove to establish the colony of Maryland at St. Mary’s City, envisioning a society based on religious freedom. Kent County was officially founded in 1642, and the earliest land patents were granted on Eastern Neck, Grays Inn Creek and Langford Creek, to men such as Thomas Ringgold, Thomas South, and Thomas Hynson. The first court was held in the home of Joseph Wickes on Eastern Neck, and the first courthouse erected in the town of New Yarmouth in 1679.

Establishment of Maryland and Kent County

People first arrived on the Eastern Shore about 12,000 years ago, shortly after melting glaciers from the last Ice Age flooded the ancient Susquehanna River valley to form the Chesapeake Bay. Using the Chesapeake’s vast watershed as a liquid highway, they hunted a variety of mammals and waterfowl; caught sturgeon, bass, shad and herring; harvested oysters, clams and mussels; gathered nuts, berries, and tuckahoe (arrow arum); and developed an extensive network of trade thousands of years before the Europeans arrived.

When Captain John Smith explored the Sassafras in 1608, he visited a palisaded Tockwogh village along its banks, possibly at Turner’s Creek. The Tockwoghs and the Ozinies, who lived near present day Rock Hall, were among the Algonquin-speaking peoples of the Peninsula. In addition to living off the abundant natural resources, they had begun to practice agriculture sometime around 800 BC, cultivating the three sisters of Native American farming, corn, beans and squash, along with the crop that would change their destiny: tobacco.

The first English settlement in Maryland was established in 1631 by William Claibourne on Kent Island, a site perfectly suited for trade with the Native Americans. Cecilius Calvert, the Second Lord Baltimore, studied Smith’s writings before he sent the Ark and the Dove in 1634 to establish a colony on land granted to him by the King at what is now St. Mary’s City. Kent Island was within the Calvert proprietorship and became “Kent County” in 1642. The Calverts and Claibourne soon became embroiled in a decades long clash over its ownership, fueled both by political upheavals in England during the reign of the Catholic-leaning Charles I, and by Virginia’s support of Claibourne. Lord Baltimore’s claim held.

The Land Grant System

The Maryland proprietary system offered generous land grants to settlers in exchange for a fee. Usually adults were granted 100 acres. Those who transported more than five men were granted 1000 acres and the right to name their estate. Some of those names still exist today in Kent County. The proprietary tenets of religious freedom also enticed some Quakers to move here to escape the more rigid rules of Virginia.

Settlers who survived were “seasoned” by the malarial swamps, heat and humidity. The Kent Island population slowly expanded, and in the 1650’s, Thomas Ringgold, Thomas South, Thomas Hynson and Joseph Wickes were the first to move across the Kent Narrows and up the Chester River. Patents were granted on Eastern Neck, Grays Inn Creek, and Langford Creek. Henry Morgan, a former indentured servant who had been named county sheriff, received land north to Morgans Creek (now Morgnec). The formation of present day Kent County had begun.

Early Settlers

In 1675, Samuel Tovey and James Ringgold laid out the town of New Yarmouth at the mouth of Gray’s Inn Creek. A courthouse was erected, along with mills, a church (St. Peter’s, now gone), taverns and, in response to pressure from the Maryland Assembly, a port. They wanted to establish central shipping points where they could control trade and levy duties.

Chesapeake settlements revolved around plantation life, rather than towns. Farms became hives of activity, cultivating tobacco and food crops; making barrels, ropes and cloth; loading and unloading cargo shipped directly abroad from their own wharves. Water was the main source of transportation, although roads began to replace paths between plantations in the 1670’s, and ferries and bridges were built at the river crossings.

Indentured servants, bound to service to work off a debt or in exchange for transportation to America, made up the bulk of labor through the 1600’s for the tobacco-based economy. Many came to realize their dream of landownership and some, like Henry Morgan, a place in society. By the late 1600’s Africans, captured and enslaved, were being imported in increasing numbers; later, a free black population slowly began to emerge.

As the 17th century drew to a close, shifting political boundaries and tobacco markets eventually led to the abandonment of New Yarmouth. But the tough, enterprising little Kent County had begun a diversification of crops and trade that would place it as a center of economy and culture in the Colonial world.

The links below are to some of the catalog records of historic site surveys contained in our research library pertaining to this time period.  Please visit our library (Wed-Fri, 10-3) for further information and photographs on these properties.  Many of these records are also accessible through the Maryland Historical Trust, in their Maryland Inventory of Historic Properties, found online at These site surveys are the product of a significant site documentation project conducted in the 1980s through a partnership of the Historical Society of Kent County, the Town of Chestertown, Kent County, and the Maryland Historical Trust.  Following this survey, the Historical Society produced and published Historic Houses of Kent County, an unequaled work of architectural history, now in its second printing and available for purchase through the Society.

Wickliffe (site), 1659

White House Farm or Stepney, c. 1690

Cedar Point Farm (site), 1693

Quaker Meeting House, 1694

Carville Hall, c. 1695

Archives of Maryland
Provides access to over 471,000 historical documents that form the constitutional, legal, legislative, judicial, and administrative basis of Maryland’s government. Online access enables users to research such topics as Maryland’s constitutions and constitutional conventions’ proceedings, session laws, proceedings of the General Assembly, governors’ papers, and military records.

Nabb Research Center for Delmarva History and Culture
Website for the Nabb Center at Salisbury University with online guides to their ever-growing databases, articles and collections on Delmarva

Captain John Smith 400 Project
A project of Sultana Projects in Chestertown

Captain John Smith National Historical Trail

Captain John Smith 
Biography of John Smith from the Historic Jamestowne and Jamestowne Rediscovery website

James Ringgold, Augustine Herman, Thomas Hynson, Richard Tilghman, Robert Vaughan, Joseph Wickes and Simon Wilmer
Biographies of several Kent Countians from the Percy Skirven article,
“Seven Pioneers of the Colonial Eastern Shore” in Maryland Historical Magazine, Vol. 15:1 (1920).

Land Records
Portal to finding land records from the Maryland State Archives website.

Kent County Court Records
Guide to“17th Century Kent County Court Records” by Alexa Cawley from the Nabb Research Center.

St. Paul’s Parish
“Old St. Paul’s Parish” from History of Kent County, Maryland, 1630-1916 by Fred G. Usilton. Includes information on New Yarmouth.

New Yarmouth
“New Yarmouth,” article by Peregrine Wroth from Maryland Historical Magazine Vol III: 1 (1908)

History of Kent County
Full text of History of Kent County, 1630-1916 by Fred G. Usilton

St. Paul’s Parish
Website for the active Episcopal Parish, established in 1692.

17th Century Kent Marriages
List of Kent County Marriages from 1654-1676

Old Kent
Full text of Old Kent: The Eastern Shore of Maryland by George A. Hanson, 1876 with index.

Cecil Calvert
Portrait of Cecilius Calvert. Maryland State Archives.

Native American
Native American image from John Smith exploration map

John Smith
Engraving of John Smith, c. 1616

The Early Indians of Kent County– Elizabeth G. Duvall


The Colonial Era

Introduction: After the founding of Chestertown as a port in 1706, Kent County became firmly established as a center of farming, trade, travel and culture within the region. Skilled craftsmen set up shop in the new town, taverns thrived as centers for news and politics, and merchants profited from Chestertown’s rapid growth. Horse races, theater and balls brought ladies and gentlemen, as well as students from Washington College, to town. In the outlying areas, mills, shipyards, plantations and water crossings were centers of activity. Although roads were poor, the shortest route between Virginia and Philadelphia brought travelers through the county, across from Annapolis on the Rock Hall ferry. By the time of the Revolution, Kent County was poised to take a position of prominence as a political and supply hub during the war.

Founding of Chestertown

In 1706, Chestertown was founded under the Act for the Advancement of Trade and the Erection of Ports and Towns. The “New Town” was laid out along the Chester River on land belonging to Thomas Joyce, once part of Simon Wilmer’s “Stepney.” The Act spurred town growth and diversification by exempting skilled craftsmen from taxes for four years if they moved into the town. It also said that all orphaned males must only be apprenticed to town craftsmen.

By the 1730’s, Chestertown was thriving. Kent County’s enterprising class of planter-merchant families, many now in their third generation, were not only skilled in maritime trade, but also were the first to lead Maryland planters away from the fluctuating market of soil-exhausting, labor-intensive tobacco, into a grain-based, more diversified economy. Their sleek, locally built craft—single-masted sloops and two-masted schooners—slipped from the harbor at the end of High Street, carrying flour, salted pork and tobacco to the West Indies, Spain, the Azores and Madeira, and returned with fruit, wine and salt. Warehouses and commercial buildings were built, as well as the solid brick manor houses still in evidence today.

Many residents, now newly prosperous, began to complain of the old ways: “…Swine are so numerous that they break into warehouses where grain is stored, and the inhabitants cannot preserve their gardens from being destroyed by them.” New laws were passed so that livestock could no longer roam freely in the New Town of Chester.

Colonial Travel

Colonial Kent County offered the shortest route between Virginia and Philadelphia, and on to points north. Travelers crossed the Bay from Annapolis on the Rock Hall ferry, rode or took a stage through thriving wheat fields, by farms and mills, past old St. Paul’s, into Chestertown for a night’s rest, then on past Shrewsbury Church, through Downs Crossroads (Galena), then crossed on another ferry at Georgetown and on into Delaware.

Traveling in the colonies was rough; early roads were often no more than wide, muddy paths and few ferry crossings offered shelter to the traveler from whipping winds and rain.

Nevertheless, our Founding Fathers made the trip often. George Washington, Thomas Jefferson, James Madison, and Patrick Henry all traveled through Kent County on their way to make history.

George Washington Slept Here

The Father of our Country made eight trips through Kent County. The first was in February 1756 to see Governor Shirley of Massachusetts; and the next year, he went to visit Virginia governor Lord Loudon in Philadelphia. Both journeys were to ask for a royal commission in the British army rather than that of a lower ranking Colonial officer. The fact that he was unsuccessful in this mission may have influenced his next two trips through Kent County.

Washington’s 1773 trip through the Eastern Shore was a personal one. He was on his way to enroll his stepson at King’s College in New York. From Washington’s diary entries we learn that on “13 [May]. After Breakfast & abt. 8 Oclock set out for Rockhall where we arrivd in two hours & 25 Minutes. Dind on board the Annapolis at Chester Town & supped & lodgd at Mr. Ringolds.” This was the  Hynson-Ringgold House on Water Street, where his hosts were Thomas Ringgold IV and Mary Galloway Ringgold.

In the fall of 1774, Washington attended the First Continental Congress in Philadelphia. Arriving at Rock Hall on September 2, he “lodged at New Town on the Chester.” The next day he rose early to “Breakfast at Down’s (Galena).” On the return trip on October 28, Washington once again “dined at Down’s & lodged at New Town upon Chester.”

Perhaps Washington’s most famous visit to Kent County occurred on May 19, 1784. He stopped in Chestertown on his way home from Philadelphia to join the Board of Visitors and Governors of the College that bore his name, and was honored by the students, faculty, board and townspeople before departing early the next morning for Rock Hall and eventually Mount Vernon.

Washington’s last trip occurred in September 1791 during a Presidential tour of the South. He dined and lodged at Worrell Tavern in Chestertown, and then traveled to Rock Hall to take a boat across the Bay. As he records in his Diaries, the “night being immensely dark with heavy and variable squalls of wind—constant lightning & tremendous thunder” the ship ran aground twice, before finally reaching Annapolis. He never came to Kent County again.


Taverns or “ordinaries” played a key role not in only travel, but also in community and political life. In them, news and gossip were exchanged, politics discussed, business conducted, and sometimes wars plotted. The taverns provided points of connection within the Colonial world.

Establishments that welcomed residents and travelers in Kent County with a blazing fire and a stiff drink included the Rock Hall Inn, (which may have given the town its name), and Daniel Toas’ ordinary at the Head of Chester (Millington). In Chestertown there was Worrell’s; Nicholson’s (now the White Swan Tavern); and the infamous Dougherty’s on High Street.

As a visiting Scot wrote in 1744: “…[I] reached Newtown and put att Dougherty’s, a publick house there. I was scare arrived when I met severall of my acquaintance …and dined att the taveren where I was entertained by the tricks of a female baboon in the yard…and treated by Captain Binning of Boston with a bowl of lemmon punch…whiele we put about the bowl, a deal of comicall discourse passe’d in which the landlord, a man of a particular talent att telling comic storys, bore the chief part.”

Henry Philips was an enterprising African American businessman who had originally purchased his freedom from Thomas Smyth. He had a license to sell “good West Indian rum, good cider, and Madeira wine,” at a concession for the popular horse races at Downs Crossroads.

Colonial Laborers

Country life centered around mills, shipyards, water crossings and plantations. Hired free men and women, bond servants and slaves were all engaged in enterprises such as planting, weaving, carpentry, smithing, animal husbandry and dairy work. While some planters operated their own mills to process local wheat into flour (which shipped better than the grain), Radcliffe Mill outside of Chestertown was run by James, a slave of Rebecca Wilmer. James was promised freedom in Wilmer’s will, on the condition that he continue to operate the mill for her family.

The sale of men and women and their services was a constant of the Chesapeake’s early economy. The sales included not only slaves, but also indentured servants and convict labor. Throughout the 1700’s, Maryland and Virginia imported more slaves than any other mainland British colony; in Chestertown, slaves were still being imported as late as 1770. After importation was outlawed, the Eastern Shore became a major supplier of slaves, since any man, woman or child who had been born into slavery was considered private property.

Of the 30,000 convicts who came to the North American mainland between 1718 and 1776, more than two-thirds came to the Chesapeake. Between 1746 and 1776, more than one-quarter of all immigrants to this area were convicts. Like slaves, they were bought and sold at auction, and any runaways were hunted down and punished.

Trades and Crafts

As the economy shifted from the import of European goods to the fledgling colonies, to the self-sustaining production of American goods, skilled workers became more commonplace, and a strong middle class evolved. In Chestertown, as in Philadelphia and Annapolis, cabinet and furniture makers, silver smiths, clockmakers and other craftsmen began to supply many of the fine pieces once available only through British trade.

Blacksmiths, rope makers, barrel makers, carpenters and dry good salesmen enhanced the local economy. Many engaged in multiple enterprises. James Piper was not only a merchant and clockmaker, but also ran a tavern, a store and a ferry service to Baltimore.

Powerful planter-merchants owned, and sometimes built, their own ships, working closely with merchants in Baltimore, Annapolis and Philadelphia. The homes of such influential figures as Thomas Ringgold and Thomas Smyth still stand today. These men and their colleagues would become significant players in the American Revolution.

Colonial Culture

Chestertown became a Colonial center of cultural activity as well as trade. Kent County residents and visitors enjoyed theatrical performances that included “The Beggars Opera” and “The Lying Valet,” and “David Douglass and His Company of Comedians.” Soon after its founding, Washington College inaugurated a tradition of public performances, including Gustavus Vasa for the 1784 visit of George Washington.

Purse and cup horse races were staged in fall and spring. Horse racing was a popular Colonial sport, drawing large crowds from surrounding towns with some people traveling from as far away as Philadelphia to enjoy the festivities. Dress balls were held in which both ladies and gentleman appeared in the latest elegant fashions. A portrait of the Colonial society can be found in the letters of Molly and Henrietta Tilghman of Chestertown, written in the 1780s.


After an “Act for the Service of Almighty God and the Establish of the Protestant Religion” established the Church of England as the official Faith of Maryland in 1692, the vision of religious freedom for Catholics, Quakers, Puritans and Presbyterians of the colony began to erode. All property owners were now taxed quantities of tobacco for the support of the Anglican Church and its clergy.

On the eve of the Revolution, the required oath of allegiance by Anglican clergy to the British Crown caused obvious difficulties for the church. William Smith, the founder of Washington College and rector at Chester Parish (now Emmanuel Church) played a leading role in a series of conventions of Maryland clergy held in Chestertown, Baltimore and Annapolis in the 1780s, from which the Protestant Episcopal Church emerged.

At the same time, Methodism was on the rise on the Eastern Shore. The Methodists’ scorn for vanity made them natural opponents of the planter class, and at their 1784 Conference, they voted to join with the Quakers in the abolition movement. (The Quakers had been called to free their slaves as early as 1778.) Later, Methodists would turn their back on the abolitionist movement as entrenched bigotry began to cause their membership to decline. Meanwhile, African American Methodists established their own churches.

The links below are to some of the catalog records of historic site surveys contained in our research library pertaining to this time period.  Please visit our library (Wed-Fri, 10-3) for further information and photographs on these properties.  Many of these records are also accessible through the Maryland Historical Trust, in their Maryland Inventory of Historic Properties, found online at  These site surveys are the product of a significant site documentation project conducted in the 1980s through a partnership of the Historical Society of Kent County, the Town of Chestertown, Kent County, and the Maryland Historical Trust.  Following this survey, the Historical Society produced and published Historic Houses of Kent County, an unequaled work of architectural history, now in its second printing and available for purchase through the Society.

St. Paul’s Church, 1715

Bedingfield Hands House, 1750

Lamb’s Meadow, c. 1733

Godlington Manor, c. 1725

White House Farm, 1721

Marrowbone, c. 1720s

Buck-Bacchus Store, c. 1735

Dougherty’s Tavern, 1740s
Also called Dougherty-Barroll House

Huntingfield (or Ellendale), 1722

White Swan Tavern, c. 1733

Worrell’s Tavern, 1758

Gilpin’s Mill, 1760

Violet Farm, 1762

Emmanuel Episcopal Church, 1768

Wallis-Wickes House, c. 1769

Colonial Kent County 
“Kent County” in Maryland’s Colonial Eastern Shore: Historical Sketches of Counties and of Some Notable Structures by Swepson Earle

Craftsmen in Colonial Kent
Article “Economic Roots of Craft Dynasties in Eighteenth Century, Maryland,”
by Christine Daniels in the book American Artisans: Crafting Social Identify, 1750-1850

Farming and Plantation Management
Gresham’s Laws: Labor Management on an Early-Eighteenth Century Chesapeake Plantation” by Christine Daniels in Journal of Southern History (link to excerpt, full text available).

Chestertown in the 1700s
Chapter primarily discussing social life in Chestertown in the 1700s, from Rivers of the Eastern Shore, by Hulbert Footner

Music and Dance in Chestertown
Chapter on music and dance in Chestertown from Dance and its Music in American, 1528-1789 by Kate Van Winkle Keller, p. 279.

St. Paul’s History
Booklet, “A Souvenir History of St. Paul’s, Kent County, Maryland” by Chris Denroche, 1893

Early 1700s Kent Marriages
List of Kent County Marriages from 1699-1715

Kent County Courthouse in the 18th Century
Rendition of Kent County Courthouse in Chestertown showing the 1720 structure with the 1750 or 1798 additions, taken from Martenet’s map of Kent.

St. Paul’s Episcopal Church
St. Paul’s Episcopal Church, built 1715.

William Smith
Portrait of William Smith, founder of Washington College, from University of Pennsylvania.

The Revolutionary War

Introduction: Marylanders protested the levy of unfair taxes under the Sugar and Stamp Acts by a distant English ruler and Parliament beginning in the 1760s. These acts were repealed, only to be replaced by more fees and restrictions on trade imposed under the Townshend Acts and Tea Act. Kent County men joined in the protest, issuing the Chestertown Resolves in May 1774. Soon after, the First Maryland Convention established Committees of Correspondence and Observation in each county to organize militia units and assure compliance with non-importation and non-exportation agreements. By July 4th, the Maryland Council of Safety became the ruling body in Maryland, and moderate leaders had persuaded others to support independence. During the war, the Delmarva Peninsula provided essential supplies to the army—especially corn, wheat and flour—earning the region the nickname “Breadbasket of the Revolution.” Kent and Maryland militia units served at home, but also provided troops for the Continental Army. At the end of the Revolution, Americans had won their independence, but not without sacrifice and struggle which continued into the post-war years.

The Chestertown Resolves

On May 13, 1774, six months after the Boston tea party, a number of prominent Kent County men gathered at a local tavern to respond to the Tea Act. In an anonymous report to the Maryland Gazette, the gathering condemned Great Britain. At a second meeting on May 18th, the participants approved the Chestertown Resolves, which acknowledged their allegiance to King George III, but registered their sworn enmity to taxation without representation. In their view, the tea tax was calculated to enslave the Americans, and they pledged that any citizen found importing or purchasing dutiable tea would be stigmatized as an enemy of the liberties of America.

A Postscript to the Resolves

The above resolves were entered into upon a discovery of a late importation of dutiable tea (in the brigantine Geddes of this port) for some of the neighbouring counties. Further measures are in contemplation, in consequence of a late and very alarming act of parliament.

“The alarming Act of parliament” was likely the Boston Port Bill of March 1774. In response to the December 1773 Boston Tea Party, the British had closed Boston’s harbor until its residents paid the tea tax and reimbursed the East India Company for its spoiled goods. This would have had a significant impact on Chestertown’s merchants who traded with New England.

The brigantine Geddes was a locally built ship owned by William Geddes, Custom Inspector and local merchant. She had arrived from London on May 7. Her cargo was owned by James Nicolson, one of the signers of the Chestertown Resolves.

“Further measures are in contemplation” likely referred to the establishment of a Committee of Correspondence, with Thomas Smyth as Chairman and Thomas Ringgold and James Nicholson among its members. Their mission was to share information with similar committees throughout the colonies, and work toward the repeal of the despised parliamentary acts. In June, the Chestertown Committee proposed to “offer a subscription for the poor inhabitants…(of Boston) who may be distressed by the stagnation of business.” Samuel Adams replied, “We cannot but applaud the spirit and determined virtue of the Town of Chester…(which) bodes well for the liberties of America.”

Legend has a band of citizens marching down the street to board Geddes and dump the tea into the Chester River on May 23. No documentation has been uncovered to definitively support this, although it is possible that there was a ceremonial dumping of the tea. On May 24, 1774, Geddes sailed to Madeira.

Kent Supplies the War Effort

The Delmarva Peninsula supplied as much as one-fifth of the wheat and flour and one-half of the corn received in Philadelphia in 1774. Wheat shipments from the Chester River district equaled those of the entire western shore above Annapolis, and Chestertown alone exported two and one-half times more wheat than what was produced on the rest of the Eastern Shore. The Continental Army made heavy demands on Maryland farmers for ships, boats and wagons to transport men and supplies.

Each county additionally was responsible for organizing and outfitting militia companies to protect against invasion and to support the Continental Army. The Council of Safety feared that an attack would take place before they were fully prepared and that communication via the Chesapeake Bay between the Eastern and Western Shores might be cut off. As a member of the Committee of Observation, Thomas Smyth spent considerable time contracting with local suppliers for the militia.

Fortunately, Chestertown had numerous skilled craftsmen eager to assist the war effort and profit as well. Food, salt, tent fabric, even arms and ammunition were in short supply and when available, these items were costly. There was little cash available for purchases and most citizens were skeptical of state paper money. Supplies sent out by ship also risked being seized by British vessels plying the Bay and Atlantic coast. For this reason, merchants and militia commissaries alike hailed the formation of the Maryland State Navy, which went into service by the end of 1776.

Revolutionary Leaders

Although Kent County was never the site of conflict during the American Revolution, it produced more than its share of Revolutionary heroes. Kent County men were among the Maryland 400, five companies of Kent County native William Smallwood’s battalion. They not only fought in the Battle of Long Island, the first major battle of the Revolution, but also stood as a final anchor of a crumbled American front line, heroically charging the British six times to give Washington time to withdraw his troops. Washington, in recognition of their gallant performance, included the remaining Maryland men in his rear guard where they covered the evacuation of the American force.

Colonel Donaldson Yeates of Knocks Folly, Turners Creek, served as the Eastern Shore’s Quartermaster. He and his neighbor General John Cadwalader of Shrewsbury Neck (present Kentmore Park) supplied provisions to the Continental Army, causing the region to earn the title, Breadbasket of the Revolution. Cadwalader later commanded the Philadelphia militia at the Battle of Princeton, and served on Washington’s staff at the Battles of Brandywine, Germantown and Monmouth, before retiring to Maryland in command of the local militia.

Thomas Ringgold helped draw up the Constitution for the new state of Maryland, along with Thomas Smyth, who served on the Maryland Council of Safety. Smyth financially supported the cause of Revolution at the expense of his own financial stability. He built the galley Chester, which became part of the Maryland State Navy in 1777, at his Lankford Bay shipyard, outfitting the vessel at his own cost. After the war, he was forced to sell Widehall, abandon the building of River House, (both on Water Street in Chestertown) and move back to Trumpington, his family’s estate on Eastern Neck.

James Nicholson became the highest ranking captain in the newly established navy, only to procrastinate setting sail in his frigate Virginia for almost two years. When he finally did, he ran her aground, and she and her crew were captured by the British. Nevertheless, Nicholson went on to pilot the barge carrying Washington to the 1789 inauguration.

Alexander Murray was one of the more versatile leaders of the Revolution. As Captain of the 1st Maryland Regiment, he not only saw action in the Campaign of New York and New Jersey, but also became the master of several private vessels that marauded British ships. Another naval hero, Lambert Wickes of Eastern Neck escorted Benjamin Franklin on his diplomatic mission to France, becoming the first naval officer to carry the American flag into European waters. As captain of Reprisal, Wickes also captured 20 enemy vessels.

On the final day of the Revolution, Tench Tilghman of Queen Anne’s County, as Washington’s Aide de Camp, rode through Chestertown on his way to inform the Continental Congress that Cornwallis had surrendered at Yorktown in October of 1781.


Young gentlemen could learn navigation, Greek, Latin, arithmetic and mercantile skills at the Kent County Free School, established by law in 1723. Charles Peale, the father of artist Charles Willson Peale, was an instructor there during this early period. Upon his father’s death, the younger Peale left Chestertown and went on to become the premiere portrait painter of his time, celebrated for his portraits of George Washington and other Revolutionary luminaries including Thomas Jefferson, John Hancock and Alexander Hamilton.

The Reverend William Smith, D.D., an acquaintance of Washington’s, came to Chestertown in 1780 to take over Peale’s post at the Kent County Free School and to serve as rector of Chester Parish. In the spring of 1782, he persuaded the State Assembly to charter a seminary of universal learning on the Eastern Shore, and George Washington to sit on its Board.

Washington College became the 10th college in America, and the first to be founded in the newly independent and unified states. Washington, who contributed 50 guineas to the College, joined the College’s Board of Governors in May of 1784. Other members included Maryland Governor William Paca and wealthy planter-merchant Thomas Smyth.

The links below are to some of the catalog records of historic site surveys contained in our research library pertaining to this time period.  Please visit our library (Wed-Fri, 10-3) for further information and photographs on these properties.  Many of these records are also accessible through the Maryland Historical Trust, in their Maryland Inventory of Historic Properties, found online at  These site surveys are the product of a significant site documentation project conducted in the 1980s through a partnership of the Historical Society of Kent County, the Town of Chestertown, Kent County, and the Maryland Historical Trust.  Following this survey, the Historical Society produced and published Historic Houses of Kent County, an unequaled work of architectural history, now in its second printing and available for purchase through the Society.

Customs House, 1740s

Widehall, 1769

Hynson-Ringgold House, 1770s

McHard House, c. 1770

Geddes-Piper House, 1780s

Trumpington, c. 1780s

River House, 1784

Washington College, 1782

Smith-Ringgold House, c. 1759

Radcliffe Cross, c. 1770

Simon Wickes House, c. 1780

Drayton Manor, 1770

John Reid House, c. 1775

Springfield Farm, 1770

Chesterville Store, c. 17841

Locust Hill Farm, c. 1780

Hopkins House, c. 1777

Hichingham, c. 1774

Chestertown Tea Party Festival
Website for the organization which hosts a festival each May.

Archives of Maryland
Provides access to over 471,000 historical documents that form the constitutional, legal, legislative, judicial, and administrative basis of Maryland’s government. Online access enables users to research such topics as Maryland’s constitutions and constitutional conventions’ proceedings, session laws, proceedings of the General Assembly, governors’ papers, and military records.

“Tea and Fantasy: Fact, Fiction and Revolution in an Historic American Town.”
Article by Adam Goodheart discussing whether Chestertown “tea party” really occurred. From The American Scholar, 2005. In order to access this article you will have to contact Washington College, or the C.V. Starr Center

Schooner Sultana and Colonial History
Website of the Schooner Sultana, a reconstructed 1768 vessel on which educational programs about colonial history and local ecology are conducted.

Washington College Essays 
Articles on Kent County’s historic College from their “Revolutionary College Project” website

Methodism on Delmarva
Excerpt from “The Garden of American Methodism: The Delmarva Peninsula, 1769-1820” by William H. Williams.

Agriculture during Revolution
Link to essential source on Delmarva farming during the Revolution: “Breadbasket of the Revolution: Delmarva in the War for Independence” by Charles Truitt (citation only)

Lambert Wickes
Biography of Kent’s famous son and naval hero.

Revolutionary Militia
Reenactors in colonial garb march in militia formation during the Chestertown Tea Part y Festival (HSKC).

John Cadwalader
Portrait of General John Cadwalader, a Kent Countian who helped supply the Continental Army, and his family.

Smyth Letter
Letter of Thomas Smyth to Thomas B. Hands denouncing the radical actions of the Baltimore Committee of Correspondence in April 1776 (HSKC).

Transitions in the Antebellum Period

Introduction: By the 1800’s, the era of international trade for Kent County was over. Baltimore was now the hub for shipping wheat and other products abroad. The transition from sail to steam enormously enhanced the ability of the Eastern Shore farmers and merchants to send their produce West. In 1813, Chesapeake became the first steamboat to cross from Baltimore to Rock Hall. By 1827, it was also offering service to Chestertown. Kent’s early transition to wheat and grains, and innovations in farming techniques also reinvigorated the economy and attracted newcomers such as George Burgin Westcott. “Wheat is in demand…and looking up. You may calculate on an advance price…except something unfavorable should take place abroad,” wrote William R. Stuart, a Baltimore merchant, to Joseph Wickes of Chestertown on November 13, 1829. Nevertheless, Kent County and the Eastern Shore were in a period of political transition. Wealthy landowners no longer dominated local politics on the Upper Shore, and a rising class of small farmers, merchants, artisans and laborers sought their own place in government. These tensions came to a head during the War of 1812, but continued through the years leading up to the Civil War.

War of 1812

Baltimore emerged as one of the top commercial cities in the United States in the late 1700s thanks to the productive agricultural lands throughout Maryland. But by 1807, the economic tensions with Great Britain that fueled the American Revolution flared again. Great Britain refused to recognize America as a neutral party in the European war, which led the States to declare an economic boycott that was especially devastating to wealthy farmers. This landed gentry, along with merchants and bankers, dominated the Federalist Party, which opposed the embargo and the war declared in 1812. In Kent County, the more egalitarian Republican Party made up of small farmers, merchants, artisans and laborers had risen in popularity after the war, but citizens dreaded the risks of a new war. Anxiety over skirmishes and the bombardment of Fort McHenry in Baltimore brought the anti-war Federalists temporary support, but in the end, American victory in the War of 1812 meant victory for the more “democratic” Republicans.

The threat along the Chesapeake Bay was very real. By 1813, a British blockade had nearly closed the Bay and ships constantly threatened farms and towns. In May 1813, the British were positioned at the mouth of the Sassafras River and sent a detachment of about 500 men to burn Georgetown and Fredericktown. After burning the lower part of the town, the British set fire to a brick house at the top of the hill when a woman named Catherine (“Kitty”) Knight implored them not to burn the house as there was an old woman ill inside. Kitty Knight kept protesting as the men proceeded to the next house, until finally they left. The heroic Kitty put the fires out and saved the structures that would later be known by her name.

The burning of the Capitol in Washington in August 1814 sent a wave of anxiety along both shores. Seven miles west of Chestertown, the 21st Maryland Militia under Colonel Phillip Reed was encamped near Fairlee when news reached them that a British frigate and two smaller vessels were headed toward them. British captain, Sir Peter Parker, had been ordered to prevent the militias from crossing the Bay to defend Baltimore. On August 28th, Parker landed 100 men near the mouth of Fairlee Creek and burned every building on the farm of John Waltham, the wheat in his granary and the stacks in his field. Two days later, they burned Richard Frisby’s farm and made plans to capture Colonel Reed and his men. Instead Colonel Reed learned of the surprise attack and was waiting when they arrived. The two sides met in a field belonging to Isaac Caulk. Despite being outnumbered and running out of ammunition, the Americans pushed back Parker’s men until they retreated. Over forty British were killed or wounded, with Parker among the dead.

19th Century Businesses

Although international trade declined in Kent, thriving mercantile establishments rose in Chestertown to serve the surrounding area. Thomas Eliason, Abel Reese, B.B. Perkins, Thomas Hynson and William Albert Vickers were among those who advertised clothing, dry goods, groceries, hardware and farming implements in the mid-19th century. Ladies such as Mary Perkins and Eliza Smith ran millinery shops.

African American Businessmen and Women also Prospered

Levi Rogers operated an ice cream saloon, serving oysters and terrapins in season. William Perkins owned the Rising Sun Saloon, with an “oyster room” for men only, and the “east room” for ladies and their gentlemen guests. James Jones earned a reputation for high quality roasts at his grocery and butcher shop. Maria Bracker owned a restaurant offering customers sponge cakes, ice cream and lemonade.

Click here to download a printable PDF of the brochure Walking Tour of African American History in Chestertown, MD 1700s to the Present.

Click here to download a PDF of the African American History Map of the Underground Railroad in Kent County and Chestertown.

The links below are to some of the catalog records of historic site surveys contained in our research library pertaining to this time period.  Please visit our library (Wed-Fri, 10-3) for further information and photographs on these properties.  Many of these records are also accessible through the Maryland Historical Trust, in their Maryland Inventory of Historic Properties, found online at  These site surveys are the product of a significant site documentation project conducted in the 1980s through a partnership of the Historical Society of Kent County, the Town of Chestertown, Kent County, and the Maryland Historical Trust.  Following this survey, the Historical Society produced and published Historic Houses of Kent County, an unequaled work of architectural history, now in its second printing and available for purchase through the Society.

Levi Rodgers House, built 1740

Caulk’s Field house, built 1743
Structure near the site of the famous battle of 1814.

Rose Hill, c. 1760
Martha Ogle Forman documented life on this plantation from 1814 to 1845 in her diaries, published by the Historical Society of Delaware.

Kitty Knight House or Archibald Wright House, built c. 1773
Home which Kitty Knight convinced the British not to burn during their raid on Georgetown in 1813

McCay’s Purchase, c. 1796

Knock’s Folly, c. 1796

Locust Grove Farm, c. 1800

Napley Green, c. 1800

Methodist Meeting House, 1801

Harris House, c. 1810

Grantham and Forrest Farm, c. 1815
Benjamin Tillotson escaped from enslavement here in 1857 during a camp revival meeting. Tillotson, afraid of being sold to slave traders from Georgia upon the death of his master, plantation owner Samuel Jarman. Tillotson narrowly escaped slave catchers who relentlessly pursued him

Big Fairlee, c. 1815

Beck’s Landing, c. 1820

Reese’s Corner House, c. 1820

Brick House Farm, c. 1820

Kings Prevention, c. 1820

Fair Hope Farm, c. 1820

Gondomah, c. 1822

Fairlee Manor, c. 1825

Mitchell House, 1825

Masonic Building, 1827

Kentland, c. 1800, 1830

Shrewsbury Church, 1834

Olivet Methodist Church, 1842

The Alms House, 1847

Early Christmas Traditions
“The Yule Log:” Remembering Christmas in 18th-century Kent County,” reminiscence by Peregrine Wroth, 1858.

War of 1812 on Chesapeake
“Rediscover 1812” website with resources and information on the War in the Chesapeake region.

Fort McHenry
Fort McHenry National Monument website.

Philip Reed
Brief biography of the Lt. Colonel and U.S. Senator from Kent County, 1806-1813.

Antebellum Life in Kent 
Brief description of book, “Plantation life at Rose Hill: The diaries of Martha Ogle Forman, 1814-1845,” a valuable primary source on Kent County history (out-of-print). Originals at MD Historical Society, MS 1779.

Joseph Hopper Nicholson, Charles Smith, James Anderson, Thomas Ward Veazey, Peregrine Wroth, James Barroll Ricaud
Brief biographies on early alumni of Washington College.

Philip Reed and Caulk’s Field
Remarks given at the dedication of a memorial at Caulk’s Field in 1902.

1790 Kent County Census
Transcription of census record.

1800 Kent County Census
Full text of handwritten census records.

1810 Kent County Census
Full text of handwritten census records.

1820 Kent County Census
Full text of handwritten census records.

1830 Kent County Census
Full text of handwritten census records.

1840 Kent County Census
Full text of handwritten census records.

Monument and Flag at Caulk’s Field near Fairlee, where Kent militia defeated men from the British frigate Menelaus in 1813.

Parts of Georgetown were burned by the British in 1813.

Portrait of Philip Reed, who led the Kent County Militia at Caulk’s Field in 1813.

HMS Menelaus, captained by Peter Parker, and which anchored with several smaller ships in Fairlee Creek in 1813.

Peter Parker
Portrait of the British commander of the HMS Menelaus, killed at the Battle of Caulk’s Field.

Kent County Courthouse
Drawing from 1907 Bird’s Eye View of Chestertown showing the oldest section of the Kent County, HSKC

Armory and Market House, Chestertown
Drawing of the armory and market house from Martenet’s 1860 map of Kent County.

Cape May Saloon advertisement
Free black Levi Rodgers operated the Cape May Saloon in Chestertown in the 1840s.

Chestertown Merchants advertisement
Merchants Wilmer & Francis and Thomas W. Eliason sold merchandise of all kinds at their establishments in the 1840s.



War of 1812: In Depth

Introduction: The War of 1812 is sometimes referred to as The Forgotten War, in spite of the fact that its defining moments were some of the most memorable in U.S. history: Admiral Oliver Hazard Perry’s naval victory in Lake Erie; the invasion of Washington by the British and first lady Dolley Madison’s rescue of George Washington’s portrait from the White House; the Battle of Fort McHenry, and Francis Scott Key’s writing of a poem that became “The Star Spangled Banner”; and Andrew Jackson’s victory at New Orleans.

The War of 1812 in Kent County reflects this paradox: an all but forgotten war, but one in which residents and local militia faced some of the most defining moments in local history.  It was the only war Kent County would experience on its own soil.  During the spring and summer of both 1813 and 1814, residents faced immediate threats from the enemy as the British terrorized the Chesapeake, looting and burning farms and towns.  Kent County citizens and local militia were tested and stood their ground with ingenuity and determination during the burning of Georgetown, the rescue of the Kitty Knight House and the Battle of Caulk’s Field.

Prelude to War

Kent County in the early 19th century was no longer a primary route of travel, nor the center of international trade as it had been during the Colonial period. Land had opened up West, and overland routes were utilized instead of the Bay crossing. Local farmers, who had long given up their reliance upon tobacco, continued with a diversified, grain-based economy that had led to the county’s Colonial prosperity, but in the 1800’s goods and produce were transported to Wilmington or shipped to Baltimore, by then the third largest and fastest growing city in the U.S.

Joseph Scott’s 1807 travelogue said of Chestertown:

It contains 140 houses, 41 of them  brick, several of them built in a style of elegance…the public buildings are all of brick.  No town on the Eastern Shore possesses so many local advantages … abundance of excellent water and a fertile, well cultivated surrounding country, but the proximity of Baltimore has monopolized the trade of Chestertown…In the town are retail stores, which supply the inhabitants of the adjacent parts with West India produce, and the various manufactures of Europe. 

The Eastern Shore had begun to settle into a new era of relative isolation.  Nonetheless, local farmers and residents would have felt the impact of events leading up to the war.

American shipping and trade had been severely hindered by war between England and France.  Neither nation respected the rights of the U.S. as a neutral nation.  American attempts to counter foreign trade restrictions, such as Thomas Jefferson’s disastrous Embargo Act of 1807 which prohibited all foreign trade, proved ineffective at best.  Baltimore, in spite of the ingenuity and brashness of its many privateers, was negatively impacted, as were the farmers whose produce was to be shipped abroad, including those of Kent County.

The British practice of impressment was another motivation for war.  In need of able-bodied seamen, the British forcibly stopped and searched American vessels, looking for suspected British citizens.  In 1807 the commander of the British warship Leopard demanded to board the U.S. frigate Chesapeake; when refused, the Leopard fired upon the vessel, killing several men, and seizing four as deserters (three of whom turned out to be American citizens).  America was outraged.

The prospect of war caused tensions between the two political parties.  The Federalists, the party of John Adams and, philosophically, of George Washington, tended to be represented in New England and among wealthy property owners, while the Republican party of Thomas Jefferson was strongest in the South, and was often the party of farmers, merchants and the middle class.  The upper Eastern Shore and upper Western Shore were primarily Republican, while the lower Shore and southern and Western Maryland remained Federalist.

Kent County was in a period of political transition.  Wealthy landowners no longer dominated local politics, and a middle class sought their place in government. Many Marylanders felt the same way: when William Smith, the founder of Washington College and then of St. Johns in Annapolis, proposed to the Maryland legislature that the two colleges receive state support as the University of Maryland, Republicans refused, declaring they would not support the education of the sons of the elite with taxpayers money.

Political lines were not always so clearly drawn.  In 1797, when Federalist Michael Taney of Calvert County proposed that property requirements for voting be abolished, Republican Joseph Nicholson of Chestertown stated that it would be as foolish as allowing women and children to vote.  By 1810, property requirements for all elections and public offices were abolished in Maryland following a proposal by Federalist John Hanson Thomas of Frederick County.  However, the continued support for property requirements by the Federalist Party in general would help lead to its demise, even though its dire forecasts about going to war with England proved correct.

The Federalist Party opposed war with England, although anti-war sentiment among Maryland Federalists was not as strong as elsewhere.  Federalists were vocal in their support of England’s stand against Emperor Napoleon’s regime, which had conquered much of continental Europe.  They also declared that the U.S. was ill prepared for war because they had too small a navy, a poorly trained army and insufficient financial means.  The Republican Party felt that militia on the ground and privateers at sea were sufficient to fight a war.

The Republican War Hawks of the House of Representatives were strong advocates for war.  Young, brash, but intelligent and articulate, Henry Clay, John C. Calhoun and others represented the second generation of American statesmen, convinced of the need for the expansion of America and for national pride. Some came from the new frontier of Tenneseee, Kentucky, Ohio and Indiana, and were concerned with the British and Indian allegiances in the Great Lakes region.  A series of confrontations organized by the Shawnee leader Tecumseh was referred to as the “Anglo-Indian War” by newspapers, after it was reported the Indians were supplied with British weapons.

Declaration of War

The Declaration of War on June 18, 1812 was the closest vote on any war in U.S. history.  The primary theatre of engagement became the U.S./Canadian border; Americans felt that they had a better chance for success invading Canada then confronting the British navy at sea.  It would become apparent that the Federalists were correct that the regular forces and militia were not prepared for war. During the first year of war, American forces and their commanders blundered their way through humiliating engagements with the highly trained British regulars.  The U.S. Navy, however, proved in naval engagements in the Great Lakes that is was, ship for ship, the equal of the British, whose navy was considered the finest in the world.

The citizens of Kent County would not feel the full impact of war until the spring of 1813 when the British turned their attention to the Chesapeake.  In spite of Kent County’s Republican leanings, there would have been anti-war sentiment among the population.  Two unnamed men were detained in Chestertown in summer 1813 under suspicion of supplying the British with grain.  An Independence Day celebration that year called upon Kent County residents to stand firm against the enemy.  And, for the most part, they did.

Terror in the Chesapeake

The British invasion of the Chesapeake was under the command of Rear Admiral Sir George Cockburn, whose task  was to ruin coastal trade, destroy supplies of grain and livestock and terrorize the population in general.  With those goals before him, he headed his naval forces up the Bay.  In late April, the British reached Kent County. ” …  they made an attempt to land at the mouth of Still Point (Pond Creek), but were repulsed by the force collected on the shore; the firing could be seen and heard from Stoney Point,”  which was across the Bay in Harford County, reported the Daily National Intelligencer (Washington, D.C.).

Raids in Kent County began with a raid on Howell Point, just north of the mouth of Still Pond Creek, when H.M. S. Maidstone bombarded the shore, terrifying local citizens.  The Daily National Intelligencer reported “the frigate lies so near Howell’s Point that she has thrown some of her shot a mile into the country.  The enemy’s force, consisting of one 74 (gun ship), three frigates, two brigs, two schooners, and a number of tenders and barges, were lying from off Werton (Worton Creek) to some distance below Pool’s Island,   …a ship of war … commenced a bombardment on Simon Wilmer’s house”.  Later, the enemy landed at Plum Point, and robbed George Medford’s smokehouse, henhouse and sheep pen, and killed his cattle.  “While they were thus employed an express was sent for the militia, a party of which arrived in time to prevent them carrying off the cattle… the militia fired on the barges as they left the shore, and it is thought some of the enemy were killed”. The British continued up the Bay, plundering Frenchtown, and raiding and burning Havre de Grace.

Georgetown in Kent County was Cockburn’s next destination.  He needed to find his way up the Sassafras, but Cockburn was “frustrated by the intricacy of the river.” His solution was to land at Turner’s Creek, an active village with a granary, store and wharf.  There the British kidnapped local resident James Stavely, forcing him to pilot them up the Sassafras to Georgetown, a bustling village of 40 houses, school, Presbyterian church and shipyard, which Scott’s 1807 travelogue had described as “one of the most healthy on the Eastern Shore, that launched many very fine schooners and brigs”. That description could not have been written after the British landed.

The British sent warning with local boaters that if the town did not resist, it would be spared, and any provisions taken, paid for. But the militia had built earthworks for defense on Fort Duffy on the north side of the river and on Pearce Point Fort on the south side.  About 400 militia men opened fire, but reports were they quickly fled as the British advanced on land, and most of the civilians hid in the woods.

The British torched house after house.  Local legend has it that they spared several homes due to the actions of  Miss Kitty Knight, a local lady of esteem, who stood up to the British when they were about to burn the home of one of her elderly neighbors. Newspaper accounts say that “several homes were spared at the entreaties of the women and the aged.”  Thirteen dwellings and outbuildings, cobbler’s shop, tavern, a granary and storehouse were destroyed that day.

As Cockburn proceeded back down the river, he noted that “…what had passed at Havre and Georgetown … had its effects, and led more to hope for from our generosity than from erecting batteries …”  The British returned Stavely to Turner’s Creek where they took supplies, “leaving the people of this place well pleased with the wisdom … on their mode of receiving us.”

Chestertown residents felt the sense of impending doom in August of 1813 when the British returned, establishing a camp at Kent Island, from which they attacked St. Michael’s and threatened Queenstown.  “Chestertown must go if attacked,” read a letter to the Western Shore, “for we have not a sufficient force to repel them.”  But mosquitoes, heat and plucky Talbot County militia encouraged the British to move out of the Bay for the time being.

The tide of war was turned in September 1813 with Admiral Oliver Hazard Perry’s brilliant naval victory in Lake Erie on the Niagra, and William Henry Harrison’s defeat of the British at the Battle of the Thames outside of Detroit, during which Tecumseh was killed.

Federalists and even Republicans celebrated when Napoleon was defeated by the British and Russian allied forces in the spring of 1814.  “I rejoice with you,” Jefferson told a friend, “in the downfall of Bonaparte.” There was some hope among Federalists that this would lead to peace with England, but Republicans felt otherwise: “We should have to fight hereafter,” said Joseph Nicholson, “not for free Trade and sailors rights, not for the conquest of Canada, but for our national existence.”

With Europe at peace for the first time in 20 years, England turned its attention to the American coast of the Atlantic, occupying part of Maine in the early summer of 1814 (and welcomed by many of the residents).  But their fiercest attention would be directed at the Chesapeake and, ultimately, the primary targets of Washington and Baltimore, the home port of privateers who had been harassing British ships in both the Atlantic and Pacific before and during the war.

The Kent County Militia Takes A Stand

The British returned to Kent County in July of 1814.  “Four of their barges entered Worton Creek.  Colonel (Phillip) Reed, an old seventy sixer (Revolutionary War Veteran), happened to be on a visit to the neighborhood, he borrowed a musket and hastily collected about 20 armed with duck guns and muskets, they formed an ambuscade, and when the largest barge had fairly passed, opened a certain fire upon them, reported the Niles Weekly Register from Baltimore, before they escaped … in all possible haste – for though he (the enemy) rowed 24 oars when he entered the creek, he could man only 4 when he went out of it.”  While the  newspaper account indicates that Lt. Colonel Reed “happened to be on a visit in the neighborhood,” payroll records for the local militia indicated that Reed had posted almost 30 men, including officers and a doctor, at the mouth of Worton Creek for up to two months in 1813 and 1814, in preparation for a British invasion.  Lt. Colonel Phillip Reed, a captain in the Continental Army during the Revolution, proved a more than a competent commander of the militia.  Another Revolutionary veteran, General Benjamin Chambers of the heroic Maryland Battalion which had distinguished itself during the Battle of Long Island; Chamber’s son, Ezekiel; and James Edmundson Barroll, were among the many Kent County citizens who would stand bravely in the defense of their own soil during the summer of 1814.

The H. M. S. Menelaus under the command of Sir Peter Parker, landed at Swan Creek on August 20 with the intention of raiding Rock Hall.  Within days, a thunderstorm caused H. M. Mary to capsize at Swan Point, sinking her load of weapons and powder.  This was the same thunderstorm that had extinguished the fires burning in Washington in the August 24 capture of the city by the British.  The defense of the nation’s capital had been ill planned and poorly executed.  Virginia militia fled before the British marched into Washington.  But the Kent County militia were prepared to stand their ground.

On August 27, Lt. Colonel Reed used what might have seemed an obvious ploy to mislead the British about the size of his forces, directing his cavalry to cross and recross the water from the mainland to Eastern Neck Island on a ferry scow.  Sir Peter Parker wrote: ” I was surprised to observe the enemy’s regular troops and militia in motion along the whole coast.”

Nonetheless, the British set out to raid Fairlee. British Lieutenant Benjamin George Beynon recorded the following in  his journal: ” Early this morning we  saw several milita men in full
uniforms on the banks very near us, at ten a great many horsemen had collect round Genl. James Loyd’s House (Big Fairlee), some dismounted, and came and reconnoitered the ship to drive them we fired a blank cartridge, at which they all but smashed their rums; a shot was then fired, and they scampered off in style, but still a great many kept round the house.  To dislodge them…some of Congreves rockets…were well thrown afterwards, and some excellent shot from the 18 pdr … at five landed and …we then set fire to the house, which was nearly full of corn as well as ten outhouses … the Cavalry were latterly in three squadrons.  I offered them Battle by advancing within one hundred yards of them, and giving them a sharp and galling fire for ten minutes which must have laid some of them low; they were extremely well mounted – smashingly dress’d in blue and long white feathers in their hats.  One fire completely routed them, at dusk no one was to be seen and we all embarked much pleased with our excursion; this is by far the finest part that I have seen in America.  The house was elegant.”

The only account of slaves in Kent County being taken by the British occurred when they next raided James Frisby’s farm at Great Oak Manor (Frisby’s wife somehow convinced them not to destroy the house).  They took with them four slaves, who likely joined the several thousand slaves offered freedom and resettled by the British during the war, mostly in the Canadian provinces.

The British went on to destroy Richard Frisby’s (James Frisby’s cousin) farm, Farley.  According to Lieutenant Beynon, there they “met some blacks who told us their masters were with the cavalry.”

Another African American encountered the British when, according to British Lieutenant Henry Crease, “An intelligent black man gave us information of two hundred militia being encamped behind a woods, distant half a mile from the beach.”  Whether this was one of the slaves or another man, possibly a free black, is unclear.  Also unclear is whether this was an attempt by the black man to betray the militia or to deceive the British.  The information was inaccurate; the militia were nearly three miles inland.  Lieutenant Henry Crease recorded that the black man stated that one-fifth of the militia gathered were to be sent for the defense of Baltimore, which was also incorrect.  British midshipman Frederick Chamier later wrote that the guide’s “sincerity in our cause was very questionable.”

The Battle of Caulk’s Field

On the night of August 30, however, Reed was accurately informed about the movement of the British. They had  landed at Skidmore – which would become known as Parker Point –  and were moving in shore. Thinking that they were intending to loot and burn, Reed prepared his men “for an opportunity which I had sought for several days to strike the enemy.”  During his march, it was discovered that the British were in search of the militia.  Reed immediately gave orders to remove the camp and to countermarch and form on the “rising ground about three hundred paces to the rear – the right towards Caulk’s House, and the left retiring on the road, the artillery in the center, supported by the infantry on the right and left.”

As the 170 British marines moved ashore, along with British sailors, American pickets exchanged fire, alerting the rest of the militia.  From three miles away, Colonel Reed heard the exchange and mobilized his 174 men toward the enemy.  The Americans returned to the cornfield that belonged to Isaac Caulk and took position near their camp, taking the time to block the cutoff through the woods and stationing riflemen in ambush.  The British charged up the hill toward the militia’s cannon, and Colonel Reed ordered the men to fire, killing and wounding several British.  As the firing continued, the Americans’ ammunition began to run low.  Reed ordered the men to fall back, and planned to fight on with a few troops while the others fled to Belle Air.  But the British did not attack again.  Sir Peter Parker had been mortally wounded and died soon after being carried off the field. His body was preserved in a barrel and shipped to Bermuda for burial, to be later exhumed and returned to England.

Local legend has it that Parker’s body was taken to the nearby Mitchell House, pickled in rum by the Americans and sent back to England.  This story might have been confused with the documented story that Major Joseph Thomas Mitchell was taken by the British from his home, suspected of being the commissary general for Maryland.  Some accounts indicate he was held in England for several years.

The Battle of Caulk’s Field provided a rare victory of militia over British forces, lifting the morale of Americans far beyond the borders of Kent County.

“Huzza for the Militia!” was the headline as the actions of Kent County militia were applauded throughout the land.  Perhaps their victory bolstered the determination of the defenders of Baltimore, who prevailed through the bombardment of Fort McHenry on September 13 and 14, inspiring the words  of Francis Scott Key, which were later put to the tune of an old British drinking song, possibly by Key’s brother-in-law, Joseph Nicholson of Chestertown.

Whatever the ramifications of the actions of local militia at Caulk’s Field, there is no question that this was a shining hour in Kent County history.

The war ended as the year drew to a close.  The Treaty of Ghent was signed December 24, 1814 although was not ratified by the U.S. Senate until February 16, 1815.  News of peace had not reached the Gulf of Mexico when Andrew Jackson led a novel-worthy army of pirates, black troops, Indians and Tennessee sharp-shooters in a brilliant and highly successful defense at the Battle of New Orleans, January 8, 1815.

Nothing was gained by the war, no changes in maritime practices were mentioned in the Treaty, and all boundaries returned to their pre-war state.

The new nation moved forward.  Steamships would cross the Bay in less than 20 years. The Industrial Revolution was ahead and would transform the world within decades.  It would be 46 more years until another war, deadlier and more terrifying, would turn Americans against each other.

This list of historic sites can be associated with the War of 1812 in Kent County, although not all of the structures were built during that time period. By 1813, a British blockade had nearly closed the Bay and ships constantly threatened farms and towns. In May 1813, the British were positioned at the mouth of the Sassafras River. In 1814, British naval forces landed at Kent Island, attacked St. Michaels and Queenstown and were in Kent County by the end of the month.

William Henry & Archibald Wright Houses/Kitty Knight House (built c. 1773)
Ships under the command of Admiral Cockburn sailed up the Sassafras River late on the morning of May 6, 1813. Soldiers torched house after house on both sides of the river. Local legend holds that when they came to a brick house at the top of the hill, Miss Kitty Knight tossed the fire brand was tossed back out.  Newspaper accounts said that several houses were “spared at the entreaties of the women and aged.”

Knock’s Folly (built c. 1796)

Lathim House (built c. 1760)
As the British prepared to attach the towns of Fredericktown and Georgetown on the Sassafras River on May 6, 1813, they landed at the mouth of Turner’s Creek and forced John Stavely to serve as their pilot. After the raid and burning of the towns, they returned to Turner’s Creek, returning their guide and plundering the property of John Lathim for supplies. Turner’s Creek was an active settlement at the turn of the 19th century with over 60 people. The Lathim House and Knocks Folly are in close proximity, so it is possible either (or both) of them may have been plundered by the British in 1813.

Christ Episcopal Church I.U. (built 1860)
Lt. Col. Philip Reed, Commander of American Forces at Caulk’s Field, who was later promoted to General is buried in this church’s cemetery. The grave was unmarked until 1902, when a granite marker was placed on his gravesite which reads :” A Soldier of the Revolution and of the War of 1812.” Reed was a member of the Chester Parish of the Protestant Episcopal church and attended services at the original building on this site, St. Peter’s, which was built c. 1767.

Buck-Chambers House (built c. 1735 and 1786)
After the Revolution, this house was acquired by Benjamin Chambers, who lived there until he moved into Widehall on Water Street in 1810. Chambers was General of the 6th Brigade, Second Division of Maryland Militia during the War of 1812. During the Revolution, Benjamin Chambers had served as a lieutenant in the Maryland Battalion during the Battle of Long Island.

Dougherty-Barroll House (built c. 1743)
This structure operated as Doughterty’s Tavern during the mid-1700s before it became the private residence. of Joseph Nicholson—who along with his brothers served prominently during  theRevolutionary War—and his son, Joseph Hopper Nicholson (1770-1817). Judge Joseph H. Nicholson organized the Baltimore Fencibiles (also called Nicholson’s Fencibles), a volunteer unit. One of Maryland’s most vocal advocates for War of 1812, Nicholson introduced a resolution calling for the non-importation of British goods, which led to the Embargo Act of 1807. During the bombardment of Fort McHenry, Nicholson kept his men at their posts for 25 hours.  Nicholson was the brother-in-law of Francis Scott Key, author of “The Star Spangled Banner.” Some histories suggest that Key gave a copy of the poem to Judge Nicholson, and it was he who suggested setting it to the familiar tune, “Anacreon in Heaven” and had the poem printed on broadsides. In 1890, a copy of the poem was discovered in a desk in the Annapolis home of Col. Joseph H. Nicholson, the Judge’s son, and is now owned by the Maryland Historical Society.

Widehall (built c. 1770)
Widehall became the home of Benjamin Chambers, brigadier general of the 6th Brigade, Second Division of Maryland Militia, in 1810. The home passed to his son, Ezekiel Forman Chambers, a captain in the 21st Regiment of the militia under Col. Philip Reed, who served during the Battle of Caulk’s Field. After the war, Ezekiel was also awarded the rank of brigadier general and commended for bravery.

Hynson-Ringgold House (built c. 1743)
106 S Water St., Chestertown, MD 21620 (PRIVATE)   Hynson-Ringgold House was the home of James Edmondson Barroll (1779-1875), secretary and adjutant to the Troop of Horse

Great Oak Manor, Frisby Farm (built c. 1938)
On August 30th, 1814, James Frisby’s farm (no longer standing) on Great Oak Manor was raided by the British. The troops proceeded to the south side of Fairlee Creek to Farley, the farm of Richard Frisby located on a small bluff with a good view of British activity at the mouth of the creek. British Lt. Benjamin George Beynon reported they burned the house, outbuildings and fields, but also received information from a slave that Lt. Col. Philip Reed’s militia was encamped near by at Belle Air, now called Fairlee. The Battle of Caulk’s Field was soon to come.

Big Fairlee, Henry Waller Farm (built c. 1815)
On August 28th, 1814, Royal Navy vessels under Sir Peter Parker fired Congreve rockets at the farm and “elegant” house of Henry Waller on the west side of Fairlee Creek. The came ashore and burned his house, outbuildings and granary. A rocket shell now on display at Fort McHenry was from the Waller Farm. After the raid, Henry Waller sold his farm to Richard Frisby, whose home Farley was also burned. It was Frisby who constructed the c. 1815 dwelling.

Mitchell House (built 1825)
On September 3, 1814, the British raided the home of Major Joseph Thomas Mitchell in the early morning, waking Mitchell and his wife. Mitchell’s horses were shot and the Major taken prisoner because it was believed he was the commissary general for Maryland. In reality, he was a militia contractor for Kent County. Major Mitchell was held prisoner in England at late as 1817, according to some accounts. The current dwelling known as Mitchell House was built by Joseph T. Mitchell in 1825.

Caulks Field House (built 1743)
The field on which Kent’s most famous battle took place belonged to Isaac Caulk, on a portion of his property owned until 1812 by his uncle, John Moore. Caulk had been a captain under Philip Reed in the 21st Regiment, which had held maneuvers on the fields in the past. Initially, the engagement was called “The Battle of Moorefield or Caulk’s Field” but since has been known by the latter name. Some experts regard Caulk’s Field is the best surviving War of 1812 battlefield in America, mostly untouched by development, identifying wooded areas and ridges that still resemble the 19th century landscape.

Impressment of Sailors.

Cartoon of fight between Jeffersonian Republican Matthew Lyon and Federalist Roger Griswold on the floor of the US House of Representatives 1798.

War of 1812 Battleships.

Francis Scott Key observing the bombardment of Fort McHenry.

Bombardment of Fort McHenry during the War of 1812.

A Black Sailor in the Navy during the War of 1812.

The burning of Georgetown during the War of 1812.

Slavery and the Civil War

Introduction: As political tensions grew in the United States between the industrial North and agrarian South, Civil War loomed. In rural areas of Maryland, especially the Eastern Shore, southern sympathies were strong. Some farmers believed that slaveholding was necessary for their livelihood and feared slave insurrection. Abraham Lincoln received only 42 votes in Kent County, but that was still more than in any other Eastern Shore county. In February 1861, the Southern Rights Convention of Maryland met in Baltimore, with Chestertown resident Ezekiel F. Chambers as President, and expected secession. Other Kent Countians were against secession, seeing it as a path to economic ruin. Although Maryland never seceded, Union soldiers occupied the State throughout the war, a source of great tension. In battle, as in debate over secession, the Civil War was truly “brother against brother.” At Culp’s Hill during Gettysburg, the Union’s 1st Regiment Maryland Eastern Shore Infantry engaged the South’s 1st Maryland Infantry CSA. After the battle, northern commander Colonel James Wallace stated: “We sorrowfully gathered up many of our old friends and acquaintances and had them carefully and tenderly cared for.” The 2nd Maryland Eastern Shore Infantry included the largest single number of Kent combatants, although Kent soldiers and sailors, both black and white, Union and Confederate, fought with many other units as well. Long after the Civil War ended, bitterness over the strong-arm tactics taken by the State administration during the war remained strong.

U.S. Senator George W. Vickers

An opponent of secession during the Civil War on the local state and national level, George W. Vickers was appointed Major General of the State Militia. “Camp Vickers,” where local troops were trained, was named in his honor. Vickers had four sons, two of whom fought in the War: one for the North and the other for the South. His son, Benjamin, joined the 2nd Tennessee Regiment, and was mortally wounded at the Battle of Shiloh. On his deathbed, he married his sweetheart, Sallie Houston, the niece of Sam Houston. His father eventually managed to have his body exhumed, and returned to Kent County for burial. In 1868, Vickers was elected to the U.S. Senate, just as the impeachment trial of Andrew Johnson was getting underway. Men crossed the Bay in an iceboat to wake him in the middle of the night to inform him of his election. Vickers then rushed to Washington. Although his seat in the Senate was challenged by Charles Sumner of Massachusetts, leader of the radical forces in the Senate, Vickers was sworn in just in time to cast the deciding vote against impeachment. Later, Vickers would once again oppose Sumner over the Fifteenth Amendment, which guaranteed voting rights to all men regardless of race, and which Vickers voted against.  After the amendment passed, James Jones and Isaac Anderson, African American businessmen in Chestertown, sold square foot lots in Chestertown to black men, so they could meet the property ownership requirements and vote. Later, Kent County’s black Civil War veterans named their GAR Hall in Chestertown after the Massachusetts senator who defended their rights: the Charles Sumner Post on South Queen Street is one of the few remaining original African American Grand Army of the Republic Posts in the United States and the only one still in use.

Slavery and Escape

By 1860, almost half the population of Kent County was black, and half of those were slaves. Even so, the number of slaves in the county had decreased by more than 50 percent since 1790, for economic reasons as well as moral ones. Wheat was less labor intensive than tobacco. It is estimated that on the eve of the Civil War, 2500 of the county’s residents were enslaved. Not all Kent County residents were opposed to the abolition of slavery, but a number of leaders, including George Burgin Westcott, James Alfred Pearce and Ezekiel Chambers, did. Residents such as John Leeds Barroll were so outraged by the threat of Northern “aggression” that they were arrested and forcibly sent South through the Confederate lines for the duration of the war. In a region in which family history is so important, it is ironic that the family life of the enslaved residents was so tenuous. Love of family was often what bound slaves to their “master’s” homes, but the ever present danger of being sold and separated was often what made them flee to the Underground Railroad in the hope that abolitionists, black and white, would help them to safety. While many runaways were caught and either punished or “sold south,” many others found freedom. Perhaps the most dramatic escape was that of Harriet Shepherd who, desperate to rescue her children from the life that she had endured, boldly stole horses and two carriages from her master and simply drove out of Chestertown with her five young children and five other slaves. They escaped to Wilmington in November 1855 and eventually reached Philadelphia with the assistance of Underground Railroad conductor Thomas Garrett of Delaware. Among the best known of runaway slaves from Kent County was the author of “Life of Isaac Mason as a Slave.” Isaac Mason’s mother was a house slave of Hannah Woodland, and his father a freeman and one of Woodland’s overseers. After Woodland died, Mason’s father was able to purchase the freedom of Isaac’s mother and sisters, but Isaac was sold. His new master was a brutal man and when Isaac resisted his beatings and abuse, he threatened to sell him to the New Orleans slave trade. Mason escaped and fled North, where he married. Although now technically free, he was still in danger because of the 1850 Fugitive Slave Law, which not only offered incentives for the seizure of anyone suspected of being a runaway slave, but also made it impossible for them to have a jury trial or to testify on their own behalf.

Conductors on the Underground Railroad

All those who worked in the Underground Railroad south of the Mason Dixon Line took great risks. In June 1858, the Kent News exposed James L. Bowers, a white Quaker farmer of Still Pond, and Harriet Tillison, a free black laundress, for assisting runaways. After the article was published, Bowers was lured from his house by a mob that stripped, tarred and feathered him in front of his pregnant wife. Immediately afterward, Harriet Tillison was tarred and feathered by the same mob and the free black man who was hiding her severely flogged. Bowers identified eight men as being part of the mob that tarred and feathered him, all of them “respectable citizens,” but they were never tried. Instead, after another meeting in Chambers’ office on the day the case was to go to court, an even larger mob of leading citizens, this time armed, apprehended Bowers and forced him to leave Kent County, two days after the birth of his child. James Bower and his wife Rebecca returned to Kent County after the war, and are buried in Cecil Friends’ Cemetery near Lynch. Harriet Tillson left the area, and her eventual location is unknown. Although some residents took measures outside the law, Judge Ezekiel Foreman Chambers, U.S. Senator James Pearce, Congressman James B. Ricaud and other Kent County leaders held a meeting in Chambers’ office to “promote the better security of their slave property.” At the meeting it was resolved that: “there can be no neutrality; he that is not for us must be regarded as against us.” As a result, they pledged not to do business with any man who would “tamper with our slaves.” Follow the path to freedom in Kent County. The Underground Railroad and the Quest for Freedom Map

Slaves Join the Union Army

Hundreds of black men from Kent County escaped slavery by enlisting in the Union Army. Steamboats from Baltimore would arrive along the shore to recruit both slaves and free blacks. Learning in advance of the ship’s arrival, so many African Americans flocked to the shore that some were inevitably left behind. Women also tried to join, without success, but boys younger than fifteen were often taken. This recruitment of slaves infuriated those slave owners who had been loyal to the Union. As citizens of a border state, their slaves had not been freed by the Emancipation Proclamation of 1862. George B. Westcott and George Vickers were among those who complained that this “…unlooked for act of military power…casts a gloom and despondency over every loyal heart…” and that “partial starvation must be the inevitable result of the loss of slave labor.” The Declaration of Rights, voted upon at the Maryland Constitutional Convention on June 24, 1864, freed the enslaved people of Maryland, despite a plea by Kent County delegate Ezekiel Chambers, that Emancipation “is ruinous to the masters; and nobody can doubt that we are in the condition, some of us, of having a large amount of money invested in this species of property.”

The Liberia Movement

The Liberia colonization movement was seen as one possible solution to the injustices that slaves and free blacks encountered. Its supporters essentially believed that whites and blacks could not live together peacefully. In 1831, the Maryland Colonization Society was formed by Dr. Peregrine Wroth, who was a frequent business partner of fellow Chestertown resident Thomas Cuff, an African American. The goal of the organization was “to establish a colony of free people of color,” and by doing so, “blot the crying sin of the land, and to remove the curse which, unhappily we inherit from our fathers.” James A. Jones and William Perkins, black entrepreneurs from Chestertown, were among its supporters. At the first African-American convention, held in Baltimore in 1852, Jones stated that; “the colored man could never rise to eminence except in Africa—the land of his forefathers.” In the end the movement was not a success; only 12,000 blacks in the entire country decided to emigrate, but that number included 1,000 from Maryland. Henry Highland Garnet, who had escaped from slavery in Kent County with his family as a child, was a supporter of the Liberia movement. He first became an abolitionist while still a high school student in New York City, where he formed the Garrison Literary and Benevolent Association. After graduating from the Oneida Theological Institute, he was ordained as a Presbyterian minister and was the first black minister to preach in the U.S. House of Representatives. Garnet rose to become a prominent abolitionist, known internationally for his eloquent, forceful and often fiery rhetoric. He urged slaves to stand up to their white masters, even if it should lead to their death and made references to slave rebellion in his speeches, thereby distancing himself from Frederick Douglass and William Lloyd Garrison. When the Civil War erupted, he turned his attention to the founding of black army units and the recruitment of troops. His last wish was to die in Liberia; he was sent there in 1881 by President James Garfield to serve as the U.S. Ambassador. He died the following year and was buried in the country’s capital, Monrovia. Frederick Douglass, in spite of their disagreements, mourned his death.

The links below are to some of the catalog records of historic site surveys contained in our research library pertaining to this time period.  Please visit our library (Wed-Fri, 10-3) for further information and photographs on these properties.  Many of these records are also accessible through the Maryland Historical Trust, in their Maryland Inventory of Historic Properties, found online at  These site surveys are the product of a significant site documentation project conducted in the 1980s through a partnership of the Historical Society of Kent County, the Town of Chestertown, Kent County, and the Maryland Historical Trust.  Following this survey, the Historical Society produced and published Historic Houses of Kent County, an unequaled work of architectural history, now in its second printing and available for purchase through the Society. Stephney, c. 1850 Wilson Point, c. 1850 Moreton Hall, c. 1850 Thomas Hynson’s Store, c. 1850 George Vickers House (site), c. 1850 Lauretum, mid-1800s St. James Church, 1853 Drake’s/Dreka Mill, c. 1854 Christ Church I.U., 1860 Still Pond Methodist Church, 1853 Davis Duplex, c. 1854 Capt. James F. Taylor House, c. 1857 Rehoboth Methodist Protestant Church, 1859 Maple Grove, c. 1860 Stephen’s Farm, c. 1860 Columbia Farm, c. 1860 Brampton, 1860 Janes Methodist Church (African-American), c. 1866

George Vickers-Charles Sumner Debate on 15th Amendment Text of the debate over the 15th Amendment in the US Senate, from Great Debates in American History, (beginning on page 127). George Vickers and the 15th Amendment Excerpt from The Trial of Democracy: Black Suffrage and Northern Republicans, 1860-1910 by Xi Wang. Discussion of George Vickers’ role in 15th Amendment debate begins on page 60. Border State Unionism in Kent County “A Study of the Effect of Federal Policies on Border State Unionism in Kent County, Maryland, 1861-1865,” senior thesis by Brandon P. Righi, Washington College. Henry Highlight Garnett Washington College Petitions for State Aid “Memorial of the Visitors and Governors of Washington College to the General Assembly of Maryland,” 1868. 1850 Kent County Census-Free Full text of handwritten census records. 1850 Kent County Census-Slave Full text of handwritten census records. 1860 Kent County Census-Slave Full text of handwritten census records. 1860 Kent County Census-Free Full text of handwritten census records. Kent County Lawyers, 1851 List of lawyers from Kent from Livingston’s Law Register. Civil War Pensioners List of Pensioners from Kent County, 1883.

Henry Highland Garnet Photograph of Henry Garnet, supporter of the Liberia movement, and a former slave who escaped from Kent County

The Victorian Era

Introduction: Major changes in transportation and technology transformed the economy, society and landscape of Kent County in the late 1800’s. The railroad arrived in Kent County soon after the Civil War. Enterprising farmers soon realized that their products could now be shipped overnight to Baltimore, Philadelphia and New York. America’s canning industry, centered in Baltimore by the mid-19th century, spread to and flourished on the Eastern Shore. Farmers expanded and diversified by growing fruits and vegetables for city markets. Watermen harvested enormous numbers of fish, oysters and crabs from the Bay and rivers, and the seafood business boomed. Drawn by the beauty and bounty of the Bay’s shores, city folk flocked to the new and more easily accessible resorts at Betterton and Tolchester. Well into the 1900’s, Kent County thrived thanks to these burgeoning industries.


Although The Kent County Railroad Company was chartered in 1856, with George Vickers as president, the first train did not pull into Chestertown until February 20, 1872, delayed by the Civil War and a lack of investors. When completed, the railroad was leased to the Philadelphia, Wilmington & Baltimore Railroad. Coming off the mainline at Townsend, Delaware, it made stops at Massey, Kennedyville and Worton before reaching Chestertown. Efforts were made to continue the tracks to the Chesapeake Bay but that project was eventually abandoned. In 1900 the line was purchased by the Pennsylvania Railroad.


Following the war, the steamboats continued to connect Eastern Shore farmers and residents with urban markets. They not only carried goods and produce, but now a new kind of cargo as well: tourists. The Chester River Steamboat Company was formed in 1865 when Colonel B.S. Ford purchased the line of Henry B.Slaughter of Crumpton. Slaughter had been offering daily service along the Chester since 1860, with the boats Arrow, Chester and George Law. The new company prospered, and B.S. Ford, Corsica, Emma Ford and Gratitude were added to the fleet. They stopped at Chestertown, Rolphs Wharf, Quaker Neck, Cliffs, Spaniards Point, Spry’s Landing, Buckingham, Round Top and Deep Landing. This regular steamboat service between the Chester and Baltimore provided local farmers and watermen with a reliable form of transport for their perishable produce, rockfish, crabs and oysters. It also allowed local merchants to bring in all manner of goods and merchandise for the thriving town of Chestertown. In spite of the claim that economic collapse would follow abolition, Kent County continued to prosper.

“Chestertown is getting more like New York every day, is a common saying in our town. Houses are being built wherever a lot can be purchased – old ones being rebuilt and improved. Mechanics are so busy, that it is almost impossible to get a small job done. Certainly it does look like a city,” read the Kent News on October 27, 1866.

Among the most beloved of the Bay steamers, the Emma Giles was built for the Tolchester Line in 1887 with money raised on condition that she be named for the backer’s daughter. For the next 50 years she carried freight and livestock, while offering elegant and luxurious accommodations for her passengers. Her arrival at the country wharves was always a big event. “She looked like the Titanic when she came into the …river,” a resident was quoted in the New Bay Times. “It was the highlight of our lives.”

Victorian Resorts

The romance of the steamship era is exemplified by two Kent County resorts of the Victorian period. Betterton became a vacation spot in the 1850’s when Richard Turner built a steamship wharf on land once known as Crew’s Landing. The community that grew as a result was named after Turner’s wife, Elizabeth Betterton. Betterton boasted hotels and guest cottages; verandas with rocking chairs; a pavilion where couples danced and flirted into the night, all with a breathtaking view of the Bay. No wonder city dwellers were attracted to this “Jewel of the Chesapeake,” well into the 20th century.

Tolchester, and the Tolchester Line Steamboat Company of Baltimore, were begun in 1877 by father and son Calvin and E.B. Taggart, and further improved by W.C. Eliason, who was hired as a company clerk but rose to be president. Tolchester had a roller coaster and miniature railroad and was the most beloved of all of the Chesapeake resorts. Happy visitors were transported from the noise and crowds of the city into dreamland. When Tolchester and the Bay Belle, the last steamboat in the Bay with a regular schedule, were surrendered to mortgage holders in 1962, service to Betteron also stopped, and an era came to a close.

The James Adams Floating Theatre brought entertainment, romance, drama, comedy and intrigue to small towns from the Mid-Atlantic to Florida from 1914 to 1941, stopping at many Eastern Shore towns, including Chestertown, Crumpton and Betterton. Author Edna Ferber, intrigued by the idea of a theatre on a steamboat, visited the floating theatre at her homeport in North Carolina, and was inspired to write the novel that became one of the most influential musicals in history: “Showboat.”


Harvesting the Land and Water

Kent County farmers were continually seeking new ways to earn a living from their land. Many wheat fields gave way to orchards and, after a peach blight, to vegetables and berries. Truck farming was a term that began on the Eastern Shore. It referred to “trucking” one’s produce to market, even though the truck was often a wagon and the market a wharf.

Watermen of the Chesapeake were also versatile. They did not just fish, but harvested a variety of produce from the Bay and its tributaries: oysters, crabs, rockfish, shad, herring and striped bass. They moved about the bay, often staying for weeks in fishing shanties, or “arks,” when necessary, so they could work all year round. The 20th century brought continued expansion of the market for seafood. Rock Hall, once the first stop on the Eastern Shore for Colonial travelers, was not incorporated as a town until 1906. It became one of the major centers of the Chesapeake fish and seafood industry. “The Rockfish Capital of the World” once boasted several large retail establishments, including Hubbard’s Pier, as well as numerous related industries. An estimated 80 percent of the residents worked in the maritime trades.

Canneries began opening in the 1830’s along the Eastern Seaboard, creating the food preservation industry, of which Baltimore soon became the national center. Along with the steamboat and the railroad, this new technology completely changed the market for both the farmers’ crops, and the watermen’s catch. Canneries opened in Kent County late in the century, the first in Still Pond in 1889, although the industry would never dominate the economy here as it did on the lower shore.


The links below are to some of the catalog records of historic site surveys contained in our research library pertaining to this time period.  Please visit our library (Wed-Fri, 10-3) for further information and photographs on these properties.  Many of these records are also accessible through the Maryland Historical Trust, in their Maryland Inventory of Historic Properties, found online at  These site surveys are the product of a significant site documentation project conducted in the 1980s through a partnership of the Historical Society of Kent County, the Town of Chestertown, Kent County, and the Maryland Historical Trust.  Following this survey, the Historical Society produced and published Historic Houses of Kent County, an unequaled work of architectural history, now in its second printing and available for purchase through the Society.

Church Lane School, 1873/1921

Chestertown Fountain, 1866-1878

Asbury Methodist Church (African-American), 1879

Melitota Store, c. 1885

Brooks (Radcliffe) Mill, 1891

Medder’s Store, 1877

Stam House/Hill’s Inn, c. 1875

Melitota Store, c. 1885

Pearce House, c. 1890

Parks House, c. 1894

Reid Hall, Washington College, 1896/1929

Methodist Protestant Parsonage, c. 1896

Worton Railroad Station, c.1900

Chestertown Railroad Station, 1903

Mench Ark, c. 1929

Chestertown Armory, 1931

Old Twin Roads Gas Station, c. 1933

Oyster Buyboat Nellie Crockett, c. 1926

Rock Hall
Book advertising Rock Hall as a summer and health resort by Rock Hall Land & Improvement Company, 1893.

1880 Kent County Census
Full text of handwritten census records.

1900 Kent County Census
Full text of handwritten census records.

1910 Kent County Census
Full text of handwritten census records.

Oystering in Kent County
“Survey of Oyster Bars in Kent County, Maryland,” 1912

Invention of the Ouija Board
New York World magazine article dated 23 May 1920 telling the story of the invention of the Ouija board.

Kent County Bridges
List of Kent County bridges (most originally constructed in the 1930s) with links to more detailed information.

Kent County Railroads
List of railroad structures still standing in Kent County.

Kent County Patentees
Link to patents granted to Kent County residents dating from 1867-1912, many of them related to farming and agriculture.

Betterton and Tolchester Beach
History of Betterton and Tolchester Resorts.

Chestertown Firehouse
Early 20th century images of the firehouse in Chestertown, HSKC.

Road Work, c. 1910
African-Americans building roads in Kent County in the early 20th century, HSKC.

Women on the Farm
Martha Neale Willson of Trumpington, near Rock Hall, tends her chickens c. 1900 (Smyth-Willson Collection).

World War II to the New Millenium

Introduction: By the end of the 1920’s, Kent Countians already had begun to feel the effects of the Great Depression. Although cash poor, most rural people made do during tough times through barter, growing their own food and doing without. Some farmers went bankrupt and were forced to find other employment. Wealthy individuals from outside the area bought up farms, and some began to restore old homes. During World War II, Kent’s young men were called to serve, and a munitions plant was built in Chestertown late in the war. In 1954 a tragic explosion took the lives of nine women and one man working at that plant, but by that time the county had a small hospital where the injured were treated. Agriculture transitioned as local canneries closed, and by the 1970’s many farmers turned from truck crops to corn, soybeans and other grains milled into broiler feed. Although harvesting seafood from local waters continued to be a significant industry as well as recreational activity, over-harvesting began to threaten watermen’s livelihood up and down the Bay. In 1967, Kent County’s schools were fully integrated, bringing about the consolidation of many smaller schools within the county. At the end of the 20th century, the population and the economy of the Eastern Shore had been forever transformed.

Civil Rights in Chestertown
“Freedom Riders Come To Chestertown,” article by Sheila Austrian on Revolutionary College website.

Integration at Washington College
Article on first black students at Washington College in the 1960s

Student Life at Washington College
Series of articles on student life at Washington College primarily covering the twentieth century on the College’s “Revolutionary College Project” site.

Kent Manufacturing Co. Explosion 
Time Magazine article on the 1954 explosion at the Kent Manufacturing Co. “defense plant.”

World War II Casualties
List of Army and Air Force casualties from Kent County during World War II

Kent County Cemetery Records – A
List of burials at select Kent County cemeteries.

Kent County Cemetery Records – B
List of burials at select Kent County cemeteries.

Kent County Cemetery Records – C
List of burials at select Kent County cemeteries.

Race Relations: A Report on Integration in a Maryland Town
Parts I and II
Part III
Part IV 

Chester River Bridge, c. 1940

Aerial View of Chestertown
Chestertown Middle School and Washington College, c. 1980, HSKC

Chestertown from the Chester River Bridge, ca. 1940

Into the 21st Century

Introduction: At the beginning of the new millennium, Kent County remains rural, but continues to be a place in transition. Its 265 miles of shoreline, marinas, wildlife areas and beaches provide ample recreational opportunities for residents and tourists alike. The county’s over 100,000 acres of prime farmland provide the second highest crop output in Maryland, with commercial nursery operations representing the most valuable product. Washington College creates a strong, academic atmosphere within the community and is a major employer, along with the UM Shore Medical Center at Chestertown, Dixon Valve & Coupling, LaMotte Chemical and David A. Bramble Paving/ Construction. The Heron Point retirement community, along with the historic and collegiate atmosphere, has attracted a large number of seniors, who now number nearly 22 percent of the population. The 18th and 19th century homes and structures, community cultural and history-inspired events, historic small towns and museums, have made the county an attractive place to visit and live. Kent’s history promises to play a strong role in its future.

The links below are to some of the catalog records of historic site surveys contained in our research library pertaining to this time period.  Please visit our library (Wed-Fri, 10-3) for further information and photographs on these properties.  Many of these records are also accessible through the Maryland Historical Trust, in their Maryland Inventory of Historic Properties, found online at  These site surveys are the product of a significant site documentation project conducted in the 1980s through a partnership of the Historical Society of Kent County, the Town of Chestertown, Kent County, and the Maryland Historical Trust.  Following this survey, the Historical Society produced and published Historic Houses of Kent County, an unequaled work of architectural history, now in its second printing and available for purchase through the Society.

Kent County Quick Facts
Current information about Kent County from the US Census Bureau.

Kent County Maryland Economic Facts
Kent County Economic Development statistics and information from 2007-8.


High Street, Chestertown, c. 2000

Eastern Neck Island, c. 2000

Galena, c. 2000

Kent County Courthouse, Chestertown, c. 2000

Washington College, c. 1990

Rock Hall, c. 2000

Rock Hall, c. 2000

African American History in Kent County

Over many years, the Society invited several of its member historians to share their research on Kent County’s African American history. Their work was published in multiple issues of the Society’s Key to Old Kent. Those articles are reproduced here.

In addition, the Society initiated the annual  Legacy Day, which celebrates and highlights African American history each August. The event begins with a lecture on the First Friday in August and features exhibits in the windows and museum at the Bordley History Center. Legacy Day, now produced in cooperation with Sumner Hall, culminates with a parade and street party on the third Saturday in August. The 2019 Legacy Day theme will be Kent County’s African American churches.

Despite the difficulty in researching the overall experience of African Americans in Kent County, the following link illustrates what some historians have uncovered. For more articles please click the articles and information tab. If you have completed research or know of a source that we would like to have for our collection please do not hesitate to reach out to us.

The Key to Old Kent-A Journal of the Historical Society of Kent County Vol. 7 2013

The following are articles written under the copyright of the Historical Society of Kent County:

Black Jacks By Erin Benz- This article contains a short history of black mariners in America from the 1740s to the 1860s. 2016

Janes United Methodist Church History-1992- This article contains a brief history of Janes United Methodist Church

Historic African American Churches of Kent County -2019- This article is a product of Legacy Day 2019

Henry Highland Garnet– By Amanda Tuttle-Smith- 2020- This article is a product of the successful application of the Henry Highland Garnet escape site to the Federal Network to Freedom program.

Community, Prosperity & Resilience: African Americans in Chestertown, MD, 1700s to Present

Genealogical Articles

Family History Collections of the Historical Society of Kent County

The following names have genealogical histories housed at the Historical Society of Kent County and are available in our research library.

Ashley Corespondence
Apsley- Vol. I, II, III
Barnhhouser, Blackiston, Rasin, & Wroth
Barroll- Barroll, Morris Keene, Vol.II
Beck Benton Elbourn
Biddle: Hazel, Rolph
Blackiston: Vol. I, II
Bolton: Vol. I, II
Bordley: Vol. I, II, III
Burgess Ball Washington, William
Carpenter, Bankhead
Caulk: Vol. I, II
Chaires: Vol. I, II (MD/NC)
Chew: Vol. I, II
Chrisfield Chrisfield
Coleman, Isaiah
Coleman: Vol. I, II
Comegy Family History
Comegy, Cornelius
Comegy Vol. I
Cornelius: Vol. I, II, III, IV, V
Cosden Vol. I
Crouch Vol. II
Davis, Clyde (Finding Fathers): Vol. I, II
Dickerson: Vol. I, II (Cliff City), III (Benj. F.), IV (John Welsey & Children), Vol. V
Dickerson/Webster (Codsen Murder)
Dunn: Vol. I, II
Eads, Johnathan
Gale, Walraven Willis Plonk
Gale Vol. I
Glenn: Vol. I, II, III
Hayne: Vol. I, II (Haynes/Haynes)
Hill, Heigh
Hynson: 1. (Thomas) 2. (Joseph Daniel) 3. (Downey Hatcherson)
Hynson Vol. II
Jones: Vol. I, II
Lamb: Vol. I, II, III
Lathim, Janvier Wethered Yeates
Leeds, Lloyd, Bozman, Kerr, Chamberlaine
Massey: Vol. I, II
Pearce II, William
Perkins, William
Reed, Gen Phillip
Ringgold: Vol. I, II, Family, III
Roland, Spicer
Wallace, Robert
Wallis, Ambrose B.
Wallis Vol.
Wallis, Samuel Books 1-9
Wallis Family
Westcott, Hill: Vol. I, II
Westcott, Tilden



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